But long before he was hanging out in Vegas and www.thedailybeast.com/articles/2016/03/28/how-palm-springs-b with Dean Martin, Peter Lawford, Joey Bishop and Sammy Davis Jr., Sinatra was quite comfortable inside a bar and learned at an early age the allure of liquor. That’s because he literally grew up inside a speakeasy.

During Prohibition his father, Marty Sinatra, ran a joint in their hometown of Hoboken, New Jersey. It was called M.O.B. Assn. of All Nations. Before you jump to any conclusions, M.O.B. are the initials of the name, Marty O’Brien, which Marty Sinatra boxed under.

“The best boxers of the day were Irish,” explains Bob Foster, the director of the https://www.hobokenmuseum.org/ and curator of its current Sinatra exhibit. At the time there was “a lot of discrimination against Italians.”

It was also in his family’s bar that an eight-year-old Sinatra launched his career singing for the patrons when he wasn’t shining their shoes.

His affinity for watering holes continued well after Repeal. Before breaking through with Harry James and Tommy Dorsey, Sinatra honed his voice in spots around the area.

In the 1940s, according to Kaplan, he discovered Jack Daniel’s. (He possibly got his first taste of the Tennessee whiskey at legendary midtown New York restaurant and bar Toots Shor.) And for the rest of his life that was Sinatra’s drink of choice. “Jack Daniel’s was really it,” says Kaplan.

He preferred two fingers of Jack, three or four ice cubes and a splash of water.

By the 1950s, especially after his breakup and divorce from Ava Gardner, “he was quite capable of polishing off a fifth of Jack Daniel’s a day,” says Kaplan. “All by himself.” He also smoked three packs of unfiltered Camels Cigarettes every day.

But being around Sinatra wasn’t always easy for his friends and family, especially if he was drinking. “He didn’t get drunk, he just got mean,” says Kaplan. The alcohol “tended to bring out the demons in him.”

However, if he had a big concert or an album to record he would go into training mode. Which meant, according to Kaplan, he “cut back a little bit,” smoking just two packs a day and drinking somewhat less.

“For years, Sinatra seemed the embodiment of the hard-drinking, hedonistic swinger who could have his pick of women and who was the leader of a party-loving entourage,” wrote Stephen Holden in his obituary of the singer in The New York Times.

But later in life this persona began to catch up to him. “In many ways, he became a victim of his own image,” says Kaplan. He became “the largest of all these larger than large figures.” For years, he was forced to keep up his reputation and he even grew to hate performing some of his signature songs, including ‘My Way’ and ‘New York, New York.’

When he passed away in California in 1998 at the age of 82 he was, naturally, buried with a bottle of Jack Daniel’s and a pack of Camel Cigarettes.

It should come as no surprise that Jack Daniel’s has recently partnered with Sinatra’s estate to create a number of special editions, including the $199 Jack Daniel’s Sinatra Select. No doubt the Chairman of the Board would have approved.